Beware repeating iCloud calendar events in Mac calendar app


Summary: If you create a repeating All-Day calendar event on your Mac calendar app (which then syncs to your other Apple devices) and then try to edit the title of the All-Day event on your Mac calendar app, the edit will NOT sync across your other devices. This error prevents users from “checking off” completed events (ie. a Bill Payment calendar).
I’m a big user of Apple’s iCloud calendar on my Mac, my iPhone, and my iPad. Among other things, I use it to track my monthly bills, which are all setup as recurring All-Day events. As I pay each bill, I edit the title of that specific entry and add an ‘x’ in front. So an event called “Pay cable bill” would become “x Pay cable bill.”
Pretty simply, right? Except that last night, I discovered my edits on my Mac were not syncing to my iPhone. If you are an Apple user, try the following steps and see for yourself:
- Create a weekly recurring “ALL DAY” event on your Mac iCloud calendar. Name it “Weekly Mac” (just so we can keep track of where the event was originally created)
- Verify the event shows up on your iOS device.
- On your Mac, add an “x” in front of the first event title so that it now says, “x Weekly Mac”. When the popup message appears, select “Only this event.”
- Check the event on your iOS device. The “x” will NOT appear.
It gets worse. Let’s say you didn’t notice the syncing error, and then the following week, you decide to check off the recurring event on your iPhone:
- On your iOS device, select a future instance of the event, such as the following week.
- Add a “c” in front of the event title so that it now says, “c Weekly Mac.” Select “Only this event.”
- Check the event on your Mac. Not only does the sync happen correctly, but it WIPES OUT your very first edit (from the above steps). The first event has reverted back to “Weekly Mac.”
After spending an hour testing different variations (including changing the original location of creation), here are my conclusions:
- If you create a recurring ALL-DAY event on your Mac calendar, and this event synchronizes across your other devices, then any subsequent edits to the event on your Mac calendar will NOT synchronize.
- If you create a recurring ALL-DAY event on your Mac calendar and then edit this event on your iOS device, the sync will work. However, it will erase any edits that were made on your Mac calendar, causing those events to revert back to their original non-edited state.
- The bug does not seem to affect recurring events that have a specific start/end time. However, I discovered other similar sync bugs for these events with start/end times.
To conclude, synchronized calendars are a big productivity gain for everyone, except when they don’t synchronize. It is unfortunate that we still cannot rely 100% on our digital calendars. Like identify theft, the question is not IF disaster will strike, but rather WHEN and to what degree. Until Apple engineers resolve these issues, my only recourse is to avoid using the Mac OSX calendar app and stick to iCloud.com for my desktop calendar needs.
System specs: Macbook Pro (Yosemite 10.10.1), iPhone 5C (iOS 8.1.2), iPad 2 (iOS 8.1.2)